267. Advice from a Unicorn Founder Turned VC, the Future of the VC Landscape for Founders & VCs, and the Founder Love Metric (Tim Guleri)

Tim Guleri of Sierra Ventures joins Nick to discuss Advice from a Unicorn Founder Turned VC, the Future of the VC Landscape for Founders & VCs, and the Founder Love Metric. In this episode, we cover: Walk us through your background and path to VC What’s the thesis at Sierra Ventures? What's been your biggest influence on the firm's ethos? You've had two incredible outcomes as a founder... first question is do you think the process of building a company today is materially different than it was when you did it... if so how? We've talked a lot on the show, over the past 8 months about the effects of COVID on venture... what have been you main observations on how VCs are adjusting to investing during COVID? What do you think the new normal for startups looks like post-covid? How do you advise a founder that's in a hot space, doesn't need capital, but has inbound interest and large investment offers, maybe at inflated valuations, from tier 1 coastal investors? How do you handle situations where the product is just not a great fit for the market and the momentum is not building the way it should? You've been through the exit process this yourself and, I'd imagine, even w/ great outcomes those are some of the hardest decision one faces as a CEO... Do you have a framework or an approach to assessing whether an exit offer is strong and should be taken or whether the founder should hold out for a bigger outcome. There are a lot of factors that play into having to wind down a company...  are there any that standout that signal to you that it's no longer working and we need to face to reality? You mentioned something interesting recently pertaining to your relationship with founders and that’s that you track a metric that you dub “Founder Love”. Can you explain how you gauge and measure this? What do you think the venture industry looks like in 5-10 year